Chianti, Tuscany

Discover Chianti — Private Tours, Experiences & Custom Travel

Overview

If you have ever believed in fairy-tales and landscapes where Kings and Queens ruled beautiful country-sides adorned with vineyards and picturesque gardens at every corner, the Chianti region is for you!

Many people ask what is the "Chianti"? There are no borders here, it is an un-spoken territory, in the Tuscan countryside between Siena and Florence, that has no precise name. No name is necessary, because when you enter the borders here, you will know very clearly that you in Chianti when the names on signs like Radda - Greve - Panzano - Castellina - and many others you will see, all end with the word Chianti!

The Chianti region comprises numerous towns, all once Medieval settlements, with castles, villas, old mills, fortifications and farmsteads. Among the popular events, the Palio horse race of Siena is perhaps the best known, although the numerous smaller scale wine Festivals, markets, and concerts organized in the castles should not be missed.

Chianti is an unspoilt land with a patchwork of meadows and fields where the famous blue-violet Iris grow wild, (the flower which was chosen as symbol of Florence and used for centuries in perfumes). Articles in Terracotta are still produced by local craftsmen.

Its natural environment is its fortune: Chianti is a splendid countryside which stretches from Florence to Siena, over great expanses of vineyards resting on the hillside from where the famous red wine is exported throughout the world.

The region's game dishes of wild boar, quail and pigeon accompanied by wild mushrooms are as famous as the area's cold meats, Chianina beef and Cinta Senese pork. The countryside is also characterized by its olive groves which produce a highly acclaimed oil.

Gallery

Chianti Simple Pleasures

Chianti, Tuscany Italy

Chianti, Italy - vineyards in spring time

Experience Greve in Chianti Italy

Via ferruccio 18 castellina in chianti Italy

Map

Multi-Day Holidays Tours

Wine Estates, Culture and Fun in Tuscany and the Cinque Terre!

This 9 night/10 day tour begins in Rome and includes some of Italy's most incredible Etruscan towns, hot-springs and forgotten (though incredibly beautiful) coastal areas that few visitors to Italy ever experience. Highlights of the tour include sta...

Private

10 Days / 9 Nights

STARTING FROM

€2,960 per person

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Tuscany & Umbria: Exclusive Small Group Tour Including Florence

This deluxe small group (or private tour ) through Tuscany and Umbria in central Italy offers our guests the possibility to experience two of Italy's most beautiful wine regions as well as Florence. There are many highlights on this tour including a...

Semi-Private

7 Days / 6 Nights

STARTING FROM

€3,820 per person

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Florence, Tuscany and the Italian Riviera

A classic introduction to the must-see sites of Tuscany and Cinque Terre. From the wine-growing lands of Chianti and Val d'Orcia to the Renaissance splendour and the museums of Florence, the tour ends in the incredible natural beauty of the Italian...

Private

10 Days / 9 Nights

STARTING FROM

€5,450 per person

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Private & Small Group Tours in Chianti

Private Tour of Tuscany's Chianti Region, including Siena

Chianti, located in Tuscany, is famous for its medieval towns and red wines. A private tour allows you to customize your itinerary for a unique experience. Explore the region's beauty whether you're a wine connoisseur, history buff or just want to se...

Private

7 Hours

PRICING

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Tuscan Wine Tour from Livorno

This tour is a perfect tour for foodies and wine lovers who want to get the most out of their time in Tuscany from the port of Livorno. Chianti is a large wine producing zone in the Tuscany region of Italy and is home to some of Italy's most notable...

Private

12 Hours

STARTING FROM

€200 per person

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The Best of the Chianti: Radda, Panzano, Greve and Castellina in Chianti with Optional Wine Tastings

The Chianti region of Tuscany is truly glorious and best experienced with a local, licensed driver who knows the area.

Private

PRICING

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Truffle Hunting & Cooking Class in the Heart of Tuscany

If you're spending your holidays in Tuscany, or even just passing through, do not miss the opportunity to learn more about one of the most mysterious ingredients of Italian cuisine: The Truffle! Have fun hunting in the woods with the truffle-dogs, t...

Semi-Private

5 Hours

STARTING FROM

€190 per person

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Hotels

Italy,Tuscany,Chianti

Hotel

Relais Vignale

★ ★ ★ ★

Situated in the heart of the Chianti Classico region, halfway between Florence and Siena. The hotel...

Ostia +5 more

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Villas

Italy,Tuscany,Chianti

Villa

Villa Castrum

5-7 Beds 10-14

Air Conditioning +4 more

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Apartment

Photo Gallery

Our Featured Properties

Italy,Tuscany,Montepulciano

Apartment

Apartments Montepulciano (Tranquillo)

2 Beds 2 Baths 5

Air Conditioning +11 more

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Italy,Tuscany,Florence,San Casciano in Val di Pesa

Villa

Villa Nicola in Chianti

5 Beds 10

BBQ +12 more

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La Dimora Regale 2 featured rental property in Chianti Italy

Italy,Tuscany,Arrezzo

Villa

La Dimora Regale 2

2 Beds 2 Baths 4+2

Air Conditioning +11 more

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Italy,Tuscany,Castiglion Fiorentino

Villa

Villa Stefano: Ideal Property for Artists, Families & Large Groups in Tuscany

7 Beds 6 Baths 16

BBQ +11 more

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Italy,Tuscany

Villa

Villa Casavecchia

12 Beds 26

Air Conditioning +8 more

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Italy,Tuscany,Pienza

Villa

Villa Pienza

4 Beds 10

BBQ +10 more

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Il Nascondiglio Verde featured rental property in Chianti Italy

Italy,Tuscany,Arrezzo

Villa

Il Nascondiglio Verde

2 Beds 2 Baths 4

Air Conditioning +11 more

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Cottage Riccio featured rental property in Chianti Italy

Italy,Tuscany,Chianti,Castellina in Chianti

Estate

Cottage Riccio

Air Conditioning +7 more

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Italy,Tuscany,Chianti

Villa

Villa Castrum

5-7 Beds 10-14

Air Conditioning +4 more

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Duetto Classico featured rental property in Chianti Italy

Italy,Tuscany,Montepulciano

Apartment

Duetto Classico

2 Beds 1 Baths 4

Air Conditioning +8 more

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Cottage Talluri featured rental property in Chianti Italy

Italy,Tuscany,Chianti,Castellina in Chianti

Estate

Cottage Talluri

2.5 Beds 5

Air Conditioning +9 more

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Italy,Tuscany,Montepulciano

Villa

Villa Tanoak

Swimming Pool +1 more

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Private Transfer Routes in Chianti

Seamless connections between key destinations across the region

Rome Florence

Private Transfer

Rome Naples

Private Transfer

Rome Venice

Private Transfer

Florence Venice

Private Transfer

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Stories That Stay With You

Here's what our guests share about their unforgettable journeys

“This company really knows their stuff and recommended our family to stay longer in each location. We didn't listen to them, but wished we had in every single place we went. They recommended Sestri Levante over the Cinque Terre which was our favourite destination on our entire trip. We visited Rome where we stayed in the outstanding Hotel ”

[Read More] Sean & Veet Chapman, CGA

“The trip was great; we appreciate all the hard work you and your team invested to make our experience a once in a lifetime trip. We appreciate all the attention to the details, in particular Giuseppe spending the time and the focus with us on the road and as we were exploring your great country.”

[Read More] Leon and Michele

“Dear Guiseppe and Jesse, We just returned from our most wonderful vacation to Italy and wanted to first thank you for putting together such a wonderful trip, and second to provide some feedback for the future. Hotels 1. Hotel Sovestro in San Gimignano was wonderful. The staff were very friendly and helpful and made the first portion of ou”

[Read More] Ron and Deb Crosby

“I traveled with JoAnn West through your services, guided by Giuseppe, in July of this year. What a wonderful experience; your service is really top notch! If I return to Italy for a tour, I will absolutely use your services again and recommend you to my friends!”

[Read More] Lucretia Brower

“Jesse, There are no words to describe the fabulous time we had in Italy. Everything went as you promised. Absolutely no problems! The venues were fabulous. The guides were punctual and helpful. It couldn't have worked out better. You and your staff deserve high praise for the quality and efficiency of your work. BTW, Guiseppe was an absol”

[Read More] Jo Ann West

“I am a travel agent from Lebanon and have organized several group tours as well as individual tours of Italy with Italy Vacation Specialists. I highly recommend them as one of the very best tour operators in Italy to work with, given their professionalism and work ethic which I feel is second-to-none in the travel industry. All of the sta”

[Read More] Nicole Haddad, Lebanese Travel Agent

“In August 2018, my family of four and myself travelled from Vancouver, BC to Rome Italy and spent 3 weeks touring Italy with IVS. This company had come highly recommended by many friends and associates of ours who had used them before and indeed to say they do an outstanding job is an understatement. You can tell while being in Italy that”

[Read More] Vijaya Sunil CPA, CGA

“I am a travel agent with All About Honeymoons and I would highly recommend Italy Vacation Specialists. Jessica was wonderful in helping us plan in a last minute anniversary vacation during high season without any issues. She even checked on our clients while on vacation to make sure things were going well. I plan on using them again soon ”

[Read More] Tammy Joyce, All About Honeymoons

“I went to high school with the owner of the company who organized my honeymoon for myself and my now wife from Tokyo. We spent three short weeks seeing Piedmont and experiencing wine paradise there, then heading to Nice in France with our private driver and flying to Rome where honestly 4 days is NOT enough. They keep saying to spend more”

[Read More] Robin and Kumi Bruun, Tokyo Japan

“We're home now from the most amazing trip to Italy! I can't thank you enough for your efforts and coordination of what was without question the finest vacations I've been on to date.”

[Read More] Carol Carson